Episode 3

Gary Vaynerchuk

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Season 1

Why Gary Vaynerchuk Trusts His Heart (And His Gut)

Welcome to All Hands, a podcast where C-suite leaders talk about how smart HR and people strategy is good business strategy. In this episode, our host, Katelin Holloway talks with Gary V about his partnership with his Chief Heart Officer, Claude Silver, how he hires on intuition, and why it’s okay to make mistakes. This podcast is brought to you by Lattice.

[Music up]

“Lean into people don't expect from them. Don't think that they're lucky to even have a job. Lean into their humanity and kindness and team, that team family thing. Really. I'm glad you asked that question cause it was a challenging one for me and I really am happy with the answer right now. You know, family is different than business, but the best teams are those things. And so lean in, lean into the humanity of this time.”

Welcome to ALL HANDS by Lattice, where we believe that People Strategy IS Business Strategy. I’m your host -- Katelin Holloway. For the last decade, I’ve been a People & Culture executive at some of the internet’s most beloved startups, but my fascination with building true people-first cultures started many, many years ago. From film to tech (and a few interesting layovers in between), the one common denominator remains: I am most passionate about enabling people through belonging to create beautiful, innovative products.”

On All Hands, I talk with CEOs and other c-level leaders about how being a "people first" company is a strategic advantage. Join us while we chat with these top leaders about how a “people first” approach isn’t just good for people -- it’s good for business too.

[Music fades out]

Today I have the absolute privilege of chatting with the Chairman of VaynerX, CEO of VaynerMedia, and 5-time New York Times bestselling author -- Gary Vaynerchuk. That’s right folks, we have Gary Vee here today to serve up some tips from his experience in leading phenomenal people-first companies.

Now, I’ve been a long time consumer of your gospel, following his spitfire advice on building businesses and negotiating personal success, but he’s mostly known for your authentic ability to meaningfully motivate anyone that happens into your orbit.

I met Gary a while back and I was struck by one thing -- he was actually the real deal. He was a great storyteller - yes - and some confuse that with “schtick” -- but he was so real, so relatable, and - honestly - too raw to be fake.

Since then, I’ve paid very close attention to how he leads, how he chooses to build your businesses, and who he chooses to keep close. Not because I’m a full on creeper -- maybe just a little bit -- but because I was genuinely curious about how he deployed his gift and how it manifested itself within his organizations. So today, after many years of waiting, I finally get to have this conversation with Gary.

Katelin Holloway:  Welcome to All Hands, Gary.

Gary Vaynerchuk:  Thank you so much, Katelin. Really, that was very sweet. Thank you.

Katelin Holloway:  Of course. So now my assumption here is that some of our listeners probably have already heard the famous Gary Vee rise to success story, but I'd be remiss if I didn't ask you to please share a bit about your journey to here.

Gary Vaynerchuk:  So I'll go real fast, um, I was born in the Soviet Union. I came to America and when I was three, you know, studio apartment in Queens, multiple families, six, seven, eight family members, depending on the timing. Um, you know, really late seventies. The economy had collapsed in the U [00:02:00] S so it was a tough economy.
You know, my parents didn't speak English. It was really, really rough. And the first several years were super rough. And you know, my parents worked super hard side jobs. My mom was home with me, my sister was born right after, so it was really, really intense. And then my dad got a job as a stock boy in a liquor store and worked.
His way up and you know, very much one of my great heroes, my dad, to like make it in America. And he eventually became the manager of that store and that allowed us to move to a, at a son, New Jersey. He eventually became the part-owner of that store, and I really had kind of a middle-class upbringing though we, you know, it's funny, I made this joke, my dad the other day, we really lived lower middle class to almost borderline. We just didn't spend any money on anything. It was super hardcore immigrant style, like spend money on nothing except shelter and food. No vacations as a kid, no stuff, you know? And that led to me wanting stuff and doing it my own way, and lemonade stands, shoveling snow, [00:03:00] washing cars.
I really had back then, it was a necessity to if I wanted to keep up with the Joneses with Nintendo and action figures, and that's what I did. And you know, kind of grinded, and then eventually became really good at baseball cards, made a lot of money on the weekends in the malls in New Jersey. And then eventually my dad had his own store in Springfield, New Jersey.
He brought me into that as a kid in the family business, and I kind of learned the liquor business, retail, customer behavior. I kind of took it over operationally in my, in my late teens, early twenties went to college. But like, you know, I was a really bad student and would come home every weekend and work in the store and you know, launched winelibrary.com, one of the first e-commerce wine businesses in America, and took my dad's business from a four to a $60 million business in an eight-year period and kind of made it.
And then YouTube came out and I just started making [00:04:00] wine videos and it just clicked the way I communicated, my expertise in that subject matter, and then I started using Twitter to promote it. Then YouTube sells to Google for $1.7 billion. I go crazy and I'm like, Oh my God, wait a minute. Maybe I have a bigger neck than just selling wine. Maybe I really do know what people are doing. It was a real epiphany for me, and then I started investing and invested in Facebook and Twitter and Tumblr first, so I came out super hot.
Then I wrote a book about social media in 2009 that kind of put me on a map called Crush It, and I started giving keynotes. And that really put me on another map cause I was good at it. And then my brother graduated from college, the economy collapsed. We decided to start Vayner Media. I wanted to start a communications kind of infrastructure cause at that point in those last three years, I realized I was really good at marketing and communicating.
And that's kind of where I'm at, wrote five New York Times Bestsellers.. And a lot of other stuff.

Katelin Holloway:  You have so much, I feel like you probably even left some off the list.

Gary Vaynerchuk:  Definitely. Vayner Sports. I'm wearing the hat right now. My brother and I started a sports agency.  I'm a creative at heart, and so I'm a creative business operator, so I need a lot of side things.

Katelin Holloway:  And, and on top of all of that, you, you are family first. Is that correct?

Gary Vaynerchuk: Yeah, I mean, you [00:07:00] know, I'm very private with my family life as anybody who follows me knows. But like, yeah, I spend my weekends, I'm checked out seven weeks vacation a year, um, recitals and sporting events.
Like, I love my family, but no question I'm, I'm wildly passionate about my career. Um, As much content as I put out, that's all post-produced from an hour, a keynote or a podcast interview like this. You know, I'm spending quite a bit of time on my personal life that it's just not a comfortable place for me to share like it is for most people in the world.

Katelin Holloway:  Right, right. The only reason I ask is, is because it's there, there's more to you than, than just your, your business. You know, trying to balance and manage everything that you have going on. In addition to that, you also have these other parts of yourself and when we talk about bringing your whole self to work and blah, blah, blah, you've got a lot on the docket. Um, a lot.

Gary Vaynerchuk:  And, and, and, you know, I'm on the board of pencils of promise and charity water on behind. I'm one of the major players in this all in challenge that's caught a lot of attention right now to raise $33 million in three weeks in the US for COVID. The more altruistic kind of things I do, I tend to not promote as much. Family, you know, I don't promote as much. I don't share as much. But yeah, I think we all bring our full selves. You know, I think the reason there's a lot of humanity in the way I operate our business has a lot to do with those other aspects of my life

Katelin Holloway:  Right. Okay. So let, [00:09:00] let's focus this conversation then, just for the sake of simplicity, on Vayner Media.
So talk to me a little bit about, uh, just the mechanics. So I know what you do externally with, with that product, with that business, but how many employees do you have in VaynerMedia.

Gary Vaynerchuk: In VaynerMedia. I think we have 650-700 then Vayner X, which is all the companies. I think it's a thousand

Katelin Holloway:  Wow. And where are your offices located? I know you have several offices.

Gary Vaynerchuk: Yep. VaynerMedia is in London, Singapore, LA, and New York.

Katelin Holloway:  I had the pleasure of seeing you speak at LinkedIn talent connect, uh, last year on the main stage, and you shared something that has stuck with me. Um, and it was the first piece of business advice your father ever gave you. Do you remember what that was?

Gary Vaynerchuk: [Laughs] Oh, Oh, I was very transparent. Yes, I do. You know, my favorite thing that my dad ever taught me was spitting in his hand. That's what I just did. And your word is your bond. And that really, really helped me you know, with my reputation. I'm glad he did that. Uh, yeah. The first piece of advice was a little bit unfortunate. He, you know, my dad grew up in the Soviet Union and he, you know, he said to me as we're literally pulling up to liquor store, he's like, keep [00:11:00] an eye on the employees. The employees are your enemy. They may steal. And that really was super foreign to me because my natural state and what I've executed my whole career has completely been the opposite. But it stuck with me. And it was, it was disappointing, jarring, concerning, but he meant it. And I judged my father for a long time around it. but now I understand it because he came from a culture that was communism where everyone stole.
But it jarred me and I rarely share it because I don't love painting that light on my dad. But, um, that was it.

Katelin Holloway:  Well, the reason it stuck with me as someone who was sitting in the audience listening to you was because the way you framed it in that conversation was really about how that has inspired you to lead with empathy and compassion and how you and your father, you know, evolve that conversation over time and the way you and your addition to the company, the family business really helped change and shaped that um, over time.

Gary Vaynerchuk: Hundred percent.

Katelin Holloway:  I think that that's, that's the, you know, the grit comes from.

Gary Vaynerchuk: My dad made a video on [00:12:00] Instagram the other day and he was talking about how much he loves the staff and it was super, like, still to this day, it feels a little foreign, but you know, I'm so proud of him because the sign of a real man, real woman, in my opinion, is the ability to change your mind or admit that you were wrong.
And so I still laugh cause I'm still a little cynical like dad, but like, it's one of the great. You know, legacies for me in that business for sure. Changing the relationship between my father and his employees has been very rewarding for me.

[Music up]

Katelin: I really appreciated Gary sharing that story because I could feel how raw that was for him. This idea of reflecting and learning as you go --- changing your opinions when you realize you’re wrong, is a huge step in being a great people first leader.

[Music fades out]

Katelin Holloway:  I have a confession to make. I am completely and entirely in love with your business partner, your Chief Heart Officer. Uh, Ms. Claude Silver. She and I have been on, a [00:13:00] few screens and stages together, and in fact, once just a few weeks ago, she's someone I've admired for a very, very long time because she dares to lead heart first. So talk to me a little bit about your relationship with Claude. How did it start? When did you know it was her? I think that your journey together is equally as fascinating.

Gary Vaynerchuk:  I met Claude through a mutual friend, Gail Tifford, who was a big executive at Unilever, and that was the Chief Brand Officer at WeightWatchers. she's like, just kind of meet my friend that was looking  for more senior account people. We met in Neil's Coffee on the Upper Eastside, and within 18 seconds I knew.

Katelin Holloway: Yeah.

Gary Vaynerchuk:  I just knew, she's the employee that most reminds me of my mother that I've ever interacted with. And I hired her on the spot and she was expensive for us and senior. And she came in and she brought great energy and she was very good at her account job. And then we started having conversations about a year in of her doing HR, which was [00:14:00] super left field, but she was the, became the person I most to this day, she's the person I most trust to, handle anything that I feel like I need to handle. And that is, as you can imagine when you value the human and you value the employee relationship graph, it's, it's very, very, very powerful. And, so here's where the story takes a wild turn. So we're kind of planning, and then Claude walks in one day and he's like, I quit.
That I just completely was caught off guard back to her own ability to [00:15:00] you know emotional intelligence, and that so it was a really, really powerful and really tap. And literally, before she finished the sentence, I started the process of winning her back. You know, she left and we stayed in touch and some were about a year later, I convinced her to come back to sit on top of all of HR with this title that I came, we came up with called Chief Heart Officer. And, um, she's my true partner. She, she's more of my partner than my CFO is.
And my CFO and I have a great relationship, especially now, cause we've gone through some tough times with COVID. But she's my true partner. Like we,  that's where the decisions are being made, um, at, at her and I level. And, um, everything goes through our filter at the end of the day.
And it's been a very fruitful, tremendous relationship, um, here. And it's, it's, it's growing and the bonding is getting even stronger.

Katelin Holloway:  And Gary, that's actually the reason you're on this show. Um, a lot of our listeners are people, you know, practitioners, they're operators within organizations and, and hopefully another cohort that we have listening in, our CEO's looking to lead more like leaders like you that they admire, who are really leading people first. Can you talk to me a little bit about how you actually partner with Claude? What does it look like when it's great? How do you know when things are hurting? Talk to me about your dynamic and what the daily looks like with you two.

Gary Vaynerchuk:  So we talked through osmosis. Sometimes it's even a look. It's a random text. We check in, but for the most part, Claude knows that what I want is for her to have a pulse on every employee. How is Rick doing? What is Sally up to? Who's a bad behavior? [00:17:00] Who's not? And it ebbs and flows. Sometimes we can talk a lot over two weeks. Sometimes we can go two weeks without talking. but her role in the HR department just fundamentally different. It is literally counselor, you know, it is literally friend. It is literally, you know, investigator. She knows that I want to know who's not a nice person. It's really true. It's as simple as that. I want to know who's not and I want to get them out and obviously we want to console and over-communicate and be candorous, but, but I, to me, people that aren't nice are just completely unacceptable within our four walls, no matter what kind of producer they are. No matter how much they're bringing in value, it's just the truth of the situation.
So, you know, that's, that's kinda how I see it  and so our interactions are texts, FaceTimes, calls, meetings, and when she's got real stuff, she'll come [00:18:00] and whether it's one real thing or six kind of real things, that's when she'll ask for meetings and she goes to the top of the calendar and away we go.

Katelin Holloway: Right. And I, I've heard you say before, in a, in a tie between your, your business partners, if it's the CFO or, you know, insert any other C level person here and Claude. Claude's always gonna take the tie.

Gary Vaynerchuk: Yes. If the CFO wants to move on, somebody causes a financial permit, and this is, we've gone through some layoffs here. Like there's nothing else that's the, you know, there's no way to sugarcoat it, you know? And what's tough about being people first is there's a level of guilt when you actually do things like having to save the business cause we have liquidation issues and you have to let someone go.
That's like the worst. But that's where, you know, that's where we've had it here even during a pandemic, a liquidation financial event where the CFO has absolutely emerged to have more clout to because we need him to lean in. There's been times in the last week where [00:19:00] Claude's say overruled what was a desperately needed financial ruling.

Katelin Holloway:  Right.

Gary Vaynerchuk:  Whether that's, whether that's diversity and inclusion offsets, you know, like, right. Like we're just conscious of that. We want it to be as good as it can be. And that gets tough, right? Because you want to make sure you're not saving people just cause they're not a white male. And so you're having these really complex, very deep conversations and it all matters. Look, I'm an independent company and the buck stops with me. And if I want great balance of people, like, then that's what's going to happen. And don’t forget, these are all subjective calls. What's not subjective is how many white men and women and minorities and what, what is subjective is, is Rick better than Sally or vice versa?

Katelin Holloway:  Right.

Gary Vaynerchuk:  So, you know, you know, these are, these are challenges for all of us in a modern world. I have a funny feeling that a lot of companies are going to get out of whack with their diversity inclusion numbers now because they're just doing whatever they can to stay alive and I actually am empathetic to that. On the flip side, [00:20:00] for me, it matters even when the ship, this ship is, it's not sinking. So to me, the ship is rocky. So let's not act like it's thinking and let's hold up our morales and our morals.

I bring that up because of the audience. I'm concerned that people are going to, um, look the other way of, some of their thoughtful and proper thinking that's been built in the last couple of years because the P&L is looking ugly.

[Music up]

Katelin: Gary said what I was thinking. Values are values -- no matter what. If your company is dedicated to supporting diverse voices, that doesn’t just end because it’s not convenient.

[Music fades out]

Katelin Holloway: I’ve listened to enough of your content. And then, so I feel comfortable saying, I [00:21:00] think that we both know that, that your true culture really reveals itself when things go south and so I, I'm very curious, how has your real culture revealed itself over the last month?

Gary Vaynerchuk:  Oh, the, I mean [mouth noise]. Besides the fact that we were forced into some layoffs because of our financial liquidation situation, just the reality of the situation, like every other part has been phenomenal. I'm not a traditional big fan of work from home because I did grow up in an old school immigrant business where like that means employees are slacking off at home, I'm happy to admit that and I'm comfortable with that. I also, that's actually that, that's a little inauthentic. Like that's 20% of it, 80% of it is, I love people around each other. I love the osmosis I love that stuff. But because that's being able to be fulfilled through Zoom, like and Google Hangouts and all other, these all other platforms like, it's been great. I'm very happy with it. Outside of the fact that some of the exits have been [00:22:00] staggered, which keeps people a little bit uneasy.
It's a lot more fun to be able to say, "Hey, we got to do this" and everyone else's, you know? We just haven't been able to do that. Cause you know, we're not under stable ground, like things are changing by the second. But the culture has been great. People have been great with each other.
I love who we've been through this and I feel confident about it.

Katelin Holloway:  I can tell you only because Claude and I were on a thing the other day together and it was, it was before, your, your layoffs but I, I could feel it in her. I could feel the, the heart and the heaviness that, that she had with it. And in answering some of the [00:23:00] questions for that particular audience, the way she talked about your partnership and the conversations you were having, I really hoped for you all that.
That some of that showed through in the way you communicated with your team. Um, and the positivity that you have for what it's going to look like moving forward, I think is really powerful.

Gary Vaynerchuk:  It's a real thing. It's a challenging, real thing, but I do think that even the people that are most upset or, or even bitter, there is at least some layer of realization that this is a very generational situation.

Katelin Holloway:  Totally this, this is something we haven't seen before. And I think, I think we're all gonna come out on the backside of this as changed people there. There's no doubt about that. The way we, we operate, the way we show up and, and, and, and to be frank, what we expect of our employers, I think will shift and change. What are some things that you have experienced during the lockdown period that you're excited to bring back with you to work when things get back to quote-unquote normal.

Gary Vaynerchuk: I'm probably going to stay and work from home on Fridays, or at least once a week and have my most meaningful meetings then.

Katelin Holloway:  Yeah.

Gary Vaynerchuk:  That's just game-changing. I don't know that that's a culture shift and a half. Um, I'll probably take five to 15 to 25 less flights a year. Yeah. For moving, said, I don't need to go for the day. That's game-changing. I'm not going to be anxious to like, you know, wrap up a meeting and head into New York city traffic to make, uh, one of my kids  recitals or sporting events when now I can leave two hours earlier and do my Zooms from Starbucks or the house or the gym that they're gonna play at.
I think I'm going to meet a lot more people because the things that I thought I needed to do in person, the touchy-feely, the nuances, the way there, I moved, all those little things. I feel like I'm mastering AKA, feeling very [00:25:00] comfortable doing over FaceTimes and Zooms. So that's great. So there's a lot of that stuff.

Katelin Holloway:  Yeah. Claude was telling me something about, she is hosting open office hours or times where-

Gary Vaynerchuk: 12-12?

Katelin Holloway: Yes. Tell me about that.

Gary Vaynerchuk: Claude calls me, she's like, ah, like Claude, why don't you do 12 minutes FaceTimes with 12 random Vayner employees? It's just a context point. It'll be fantastic. And it's crushing.

Katelin Holloway: Nice.

Gary Vaynerchuk: Just a hello. Just a hello. Everybody goes around and says hi. One thing, and it makes them feel closer to Claude, which is what I'm looking to scale and away we go.

Katelin Holloway: Does Vayner media have stated values?

Gary Vaynerchuk: You're going to love this. I'm not sure. I think they, the team has done some stuff. The stated value for me is like kindness over everything.  [00:26:00] I think we're a little more osmosis. I'm a little bit less, let's make a bill of rights, but I'm not against it. I actually think most people learn well from that. That's something that I think I've, quote-unquote dropped the ball on. I think we could put clarity to it. We do have an incredible onboarding first week. You know, I have a lot employees that come to me like, wow, I really understand what I'm here for. So that's kind of cool. I'm excited about that. I don't know if that comes in the manifestation of a poster or a handbook, but I think we do articulate in the interview process and definitely in the onboarding first week.

Katelin Holloway: For what it's worth, I've seen the values thing come to life in many different ways. I worked at Pixar animation studios for a long time and we never had stated values, but I knew why I showed up every day that the mission and the vision were super clear. So

Gary Vaynerchuk: I tend to go that way cause I don't like how people interpret it. Like things that are put on paper. I'd rather be a feeling then letting the excuses of an adjective misplay it.

Katelin Holloway: Right, and you can [00:27:00] wordsmith them to death well.

Gary Vaynerchuk: Ugh-- That's why I like kindness over everything. Tough to manipulate that. Like kindness is hard to, you know, you know, you can manipulate that. Somebody could say, look, I'm tough because that's kind, I'm, I'm being candorous so like, you could play anything.

Katelin Holloway: It's, it's so true. But I think, I mean, luckily for you it's hard for people to not know what you stand for. Uh, you have so many different platforms in which you, you, you just are so authentic and your, the way you deliver and you've been consistent with time. I think, you know, having, I'm someone who's followed your content for a long time, you, you have been consistent. I think that the feds have the technology and the things that we're faced with, you know, COVID being, no, uh, you know, it doesn't sit outside of that realm, but. I think that you are great at looking forward and being futuristic in your thinking,  your core values, your human values, what you hold most dear, um, you've, you've always been consistent with, so [00:28:00] thank you. I just was curious how it showed up because every company is different and we all operate with different frameworks.

Gary Vaynerchuk: You know how it really shows up almost every meeting I have as they sit down in my office, they're like, man, this place, you can just smell it in the air.

Katelin Holloway: So I work at Initialized Capital now and I'm getting to know our portfolio. And so as I, as I walk into these different founder meetings, which are all virtual, so great time to start a new job, it's hard for me to understand that, that feeling without being there physically.

Gary Vaynerchuk: I get it. I get that.

Katelin Holloway: Do you feel like you're losing that or is it because it's your own company?

Gary Vaynerchuk: For sure. Yeah. With my own company, it's a little bit easier. And I also not overly stressed about eight weeks or 15 weeks, you know, there's a little bit of that but. Yeah. I definitely, there's, there's plenty of things that real life is better than Zoom, you know what I mean? So, you know, yes. I think that's right. Yeah.

Katelin Holloway: Okay. So If you don't have [00:29:00] stated values to kind of point to and help people stay on the rails or keep on track when you're thinking about managing performance. And my definition of performance is both your results and your behaviors that drive those results.
Um, how do you know when something is off? Um, outside of Claude, you know, knocking on your door and being like, yo, we got a problem over here.

Gary Vaynerchuk: Uh, the other eight 80 people that do the same thing with me. I'm like my ear is to the ground.

Katelin Holloway: Yeah. I think I've read once or saw you on stage once talking about how you, you intentionally invest time in, in following your employees on, on their social media channels. Do you still do that?

Gary Vaynerchuk: I do. And it, you know, because, because all of this is subjective when it comes to review time, when Karen's like, Sally's amazing, I'm like, sure, you're, you're rock climbing with her everyday. Your you and your boyfriends are best friends. Like, I need to have that because I'm the judge and the jury and I need to have context.
Not that there's anything wrong with that. I mean, some of, Brandon is my best friend. He's also the best executive ever worked with. That's why, why library's flourishing? [00:30:00] Like, you know, so. But I like to have the context, you know, uh, I, I'll give you a real life example. There was one young woman that was getting forced out of a team, the worst feedback. And I knew, cause I did some real homework watching it unfold and then double dipped in once it became an issue that that young woman properly had a problem with one other young woman. But that young woman, the second one, had been on the team for a long time and was best friends with everybody.

And then so they all subconsciously, half of them consciously, the other half of them rallied against this young woman who was a hundred percent right and our company would have and our company would have fired her.

Katelin Holloway: So what did you, what did you do?

Gary Vaynerchuk: I didn't fire her. I switched her out and I scolded everybody else for some bullshit.

Katelin Holloway: Yeah. I think that that's a really hard thing that CEOs don't invest the time in.

Gary Vaynerchuk: HR departments don't invest in talking to what I just said, nobody's investing time into that.

[Music up]

Katelin: Now, this may seem a bit much, and I know it can take up a lot of time, but this is just one example of how important it is to be involved in the people aspect of your company. But you shouldn’t do it alone -- HR teams and managers should be leaning on each other --- and not just in times of crisis.

[Music fades out]

Katelin Holloway:  How about on the hiring front? So if we go further upstream, I know that you hate references. I do too. They're bullshit. Uh, and but how, and I also think that the entire hiring process is, is busted 16 ways to Sunday.

Gary Vaynerchuk:  That's why it's why I completely guessed on intuition and then deal with it after the fact. And I'm not even kidding. And I know that that's not scalable for others. I just can't make up how I do it. My company does it however they want. We've got people that I believe in.

Katelin Holloway:  Yeah.

Gary Vaynerchuk: You know, kind of going through the hiring process, but they, but a lot of them I believe in, but they had totally different processes than me.
And I think we're too slow at hiring. I don't think we're too slow at firing. [00:32:00] Too slow at firing is my fault. Too slow at hiring is my company's fault. And we've got, you know, those are some of our vulnerabilities.

And I would say that my company's greatest vulnerability is the lack of candor that goes into sometimes firing and it's a stream we've gotten a lot better at it because I realized I wasn't good at it. I didn't like the confrontation. And so I would just do the bandaid move. And that led to a lot of hurt and I regret it, but I wasn't, I'm not good at conflict. I've gotten much, much better, but I'm still probably a five.
It's a lot better than the one that I naturally was. and I'm, and I hope to get better because, because I think as we've found our balance with candor leading to exit, it's definitely been better.

Katelin Holloway:  Do you feel like your partnership with Claude or moving somebody that once was in a marketing role into this people role, has [00:34:00] that helped your ability to, to find or have those conversations a little bit more easily? Or is this a path you've been writing on your own?

Gary Vaynerchuk:  No, cause Claude's also got the same flaw.

Katelin Holloway: Interesting.

Gary Vaynerchuk: But we're just, we're just sweet like that and, and, and that sweetness. Unfortunately, occasionally, occasionally, 20% of the time manifests into not enough feedback, the person's stunned that are fired and we're now bad people.
And I used to get mad at my employees when I was a kid. I was like, how do you not know? You stink? Like, and by the way, I've kept you here a year longer than you should have been. And like when you've stunk at other places and you need to continue to like, but then I realized I need to be more accountable in this one.
And so we've gotten better. We're still not all the way there, but we've definitely gotten better. And we're gonna continue to try to get better.

Katelin Holloway:  I mean, that's all we can do, right, is identify those weaknesses and have that self awareness. We always tell our managers, like, if it's a surprise to the person that you're letting go, that they're getting fired, then you've done something wrong, manager, and something that I've found, I'm just curious to get your thoughts on this. This might be a little bit, not well accepted in the people community, but I actually believe that the people that truly have those behavioral challenges, maybe it's not performance like as related to their job, but the behavioral performance side of the gig. Uh, they lack a deep sense of self-awareness or even a mild sense of self-awareness.

Gary Vaynerchuk: You're preaching, you're preaching.

Katelin Holloway: Of course, they're going to be surprised.

Gary Vaynerchuk: There's people we'd given 30 pieces of feedback to that are stunned.

Katelin Holloway:  Right?

Gary Vaynerchuk: And, uh, again, I think that, um, I do rely on intent. What absolutely puts me at a place where I can put my head on my pillow, is we've made many mistakes. The amount of mistakes I've made in last 22 years operating businesses at the top has been extraordinary. On the flip side, the intent was never bad. And I feel good about that. I never chose money over the human. I might've struggled in my early years and even to this day with the necessary candor to not make it, you know, to make it as great as it can be in such a crappy situation. But I'm way further along and my intent is way beyond my contemporaries. I know that to be true.

Katelin Holloway:  I also think it's funny to have that boomerang in conversation with folks later on in life. If you ever have that opportunity to be like, “Oh hey, I know I could have showed up in a different way.”

Gary Vaynerchuk: And Katelin, I'll be honest with you, I've been pretty lucky. I've had it 80% of the time where people come back and be like, "well, you know what, I, I took you for granted or I was entitled cause it was your fault I was entitled Gary because you made it so cozy. But I do appreciate you more."
I'm also always open for business on any relationship that didn't go well, like I'm always ready for somebody, including people that have stolen from me, including people that I did a bad job because they had a great run, but I stunned them with my out of nowhere firing. I am absolutely willing to have that relationship at all times because I always think yesterday is contextual, but not as important as today and tomorrow.

Katelin Holloway:  I completely agree.
So I'm gonna hit you with rapid-fire questions. I want you to try to answer them as quickly as possible. Don't overthink it. Are you ready?

Gary Vaynerchuk: Yes.

Katelin Holloway:  Is a hot dog a sandwich?

Gary Vaynerchuk: No.

Katelin Holloway:  Zoom or phone call?

Gary Vaynerchuk: Zoom.

Katelin Holloway:  Giants or Jets? [Laughs] Okay. Okay. That was just the warm up.

Gary Vaynerchuk: By the way, for anybody who doesn't know Jets over everything,

Katelin Holloway:  This is your North star. Okay? Okay. That was the warmup. These last ones won't be so easy.
Company culture, family, or sports team?

Gary Vaynerchuk: Great fucking question. Wow. Sports team with unbelievable amounts of family dynamics.

Katelin Holloway:  Oh, I like that answer. That's the best one I've gotten yet. I like that one.

Gary Vaynerchuk: Thank you.

Katelin Holloway:  Okay. What is your favorite interview question and why? So when you were interviewing someone.

Gary Vaynerchuk: What is the greatest thing that could happen out of you taking this job?

Katelin Holloway:  Ooh.

Gary Vaynerchuk: I like reverse engineering.

Katelin Holloway:  Yeah. Yeah, yeah, yeah. I like that. Okay.

Gary Vaynerchuk: And then peppering them for five, three to four minutes in that to make them tell you the actual truth, not the answer they think you're looking for.

Katelin Holloway:  Right. It's the power of why you ask it five times or whatever. Awesome. Okay. Now, the last one is actually my favorite interview question that I've asked every employer that I've ever taken a job with, and that is, when was the last time you wanted something so badly it hurt?

Gary Vaynerchuk: That's a really great question. I would say last year's national sportscard convention I couldn't sleep for two weeks cause I knew my son and I were going to go for an entire week. Set up a table and spend deep amounts of time together around a connection point we have with each other at [00:40:00] this young of an age.
And like literally, as I'm saying this to you right now, my heart is breaking because I'm pretty confident this year is going to be canceled the last week of July in Atlantic City because I literally treat it as a, as a Christmas event because it is such a bonding thing for me and him.

Katelin Holloway:  Oh, I love that. Okay, well, I would have taken the job with you. Good answer. Alright, so this is it. I am feeling so inspired by our conversation as I knew I would. Um, it is what you do best at the end of the day. So very, very last question to wrap it up here. Uh, what advice would you give to leaders and people leaders out there trying to make sense of this pandemic? How can they use this as an opportunity to build a better organization on the backside of everything?

Gary Vaynerchuk: Leaning into the humanity and your people is going to be the tactic that leads to the biggest financial success post this pandemic hundred thousand percent. Lean into people don't expect [00:41:00] from them.
Don't think that they're lucky to even have a job. Lean into their humanity and kindness and team, that team family thing. Really. I'm glad you asked that question cause it was a challenging one for me and I really am happy with the answer right now. You know, family is different than business, but the best teams are those things. And so lean in, lean into the humanity of this time.

Katelin Holloway:  I love it. Gary, thank you so much for joining me. I'm so grateful.


Katelin Holloway VO:

And to you, the listener! Thanks so much for joining me on this week’s episode of All Hands, brought to you by Lattice. I’m your host, Katelin Holloway. 

This episode was produced by Pod People: Rachael King, Eliza Lambert [AH-liza], and Samantha Gattsek [GATT-sic]. Special thanks to Annette Cardwell. Learn more about how Lattice can help your business stay people focused at Lattice DOT com or find us on Twitter @LatticeHQ. Don’t forget to subscribe to All Hands, wherever you get your podcasts.

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About the Guest

podcast guest

Gary Vaynerchuk

Gary Vaynerchuk is a serial entrepreneur and the Chairman of VaynerX, a modern day communications parent company, as well as the CEO and Co-Founder of VaynerMedia, a full-service digital agency servicing Fortune 500 clients across the company’s 4 locations. Gary is also one of the most sought after public speakers alive today.

He is a venture capitalist, 5-time New York Times bestselling author, and an early investor in companies such as Twitter, Tumblr, Venmo and Uber. Gary has been named to both Crain’s and Fortune’s 40 Under 40 lists.

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